2',4-dihydroxy-4'-methoxy-6'-O-(beta-glucopyranoside)-dihydrochalcone - Compound Card

2',4-dihydroxy-4'-methoxy-6'-O-(beta-glucopyranoside)-dihydrochalcone

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2',4-dihydroxy-4'-methoxy-6'-O-(beta-glucopyranoside)-dihydrochalcone

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Chalcone
    • Subclass: Dihydrochalcone
Canonical Smiles OCC1OC(Oc2cc(OC)cc(c2C(=O)CCc2ccc(cc2)O)O)C(C(C1O)O)O
InChI InChI=1S/C22H26O10/c1-30-13-8-15(26)18(14(25)7-4-11-2-5-12(24)6-3-11)16(9-13)31-22-21(29)20(28)19(27)17(10-23)32-22/h2-3,5-6,8-9,17,19-24,26-29H,4,7,10H2,1H3
InChIKey PQCIBORQLVRFMR-UHFFFAOYSA-N
Formula C22H26O10
HBA 10
HBD 6
MW 450.44
Rotatable Bonds 8
TPSA 166.14
LogP 0.1
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.41
Exact Mass 450.15
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Guibourtia tessmannii Leguminosae/Fabaceae Plantae 327904

Showing of synonyms

  • Fuendjiep V, Wandji J, et al. (2002). Chalconoid and stilbenoid glycosides from Guibourtia tessmanii.. Phytochemistry,2002, 60(8), 803-806. [View] [PubMed]
Pubchem: 12308643
Nmrshiftdb2: 2321

No compound-protein relationship available.

Structure

SMILES: c1ccccc1CCC(=O)c2c(cccc2)OC3CCCCO3

Level: 2

Mol. Weight: 450.44 g/mol

Structure

SMILES: c1ccccc1C(=O)CCc2ccccc2

Level: 1

Mol. Weight: 450.44 g/mol

Structure

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 450.44 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 450.44 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 450.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.82
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.21
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.11

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.86
Plasma Protein Binding
6.04
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.42
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.49
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.71
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.19
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-58.18
Rat (Acute)
2.31
Rat (Chronic Oral)
3.95
Fathead Minnow
4.28
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
537.77
Hydration Free Energy
-4.46
Log(D) at pH=7.4
0.88
Log(P)
0.12
Log S
-3.9
Log(Vapor Pressure)
-10.26
Melting Point
152.81
pKa Acid
5.33
pKa Basic
5.19
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9425
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9369
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9364
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9308
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.9141
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9120
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8976
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8955
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8917
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8801
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8670
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.8670
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8640
Precorrin-3 methylase O68097 O68097_RHOCA Rhodobacter capsulatus 4 0.8639
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8625
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8591
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8535
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8478
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8472
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8470
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8429
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8357
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.8330
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8271
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8270
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.8263
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8214
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8213
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8209
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8206
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.8189
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.8179
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8110
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.8053
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7966
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7936
Caspase-6 P55212 CASP6_HUMAN Homo sapiens 3 0.7921
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7887
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7854
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7775
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7759
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7730
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7695
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7695
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.7687
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7628
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7619
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7592
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7579
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7575
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 3 0.7561
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7549
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 4 0.7539
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7539
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.7538
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7531
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7517
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7515
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7513
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7508
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7490
23S rRNA (guanine(745)-N(1))-methyltransferase P36999 RLMA_ECOLI Escherichia coli 3 0.7474
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7473
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7436
Cellular tumor antigen p53 P04637 P53_HUMAN Homo sapiens 3 0.7435
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7430
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7418
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7417
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7404
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7402
Serine/threonine-protein kinase VRK1 Q99986 VRK1_HUMAN Homo sapiens 4 0.7398
Seed lectin subunit I P05045 LEC1_VIGUC Vigna unguiculata subsp. cylindrica 3 0.7396
Laminarinase Q9WXN1 Q9WXN1_THEMA Thermotoga maritima 3 0.7381
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7359
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7359
M17 leucyl aminopeptidase Q8IL11 Q8IL11_PLAF7 Plasmodium falciparum 3 0.7353
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7343
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7341
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7334
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7334
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7328
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7311
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7306
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7305
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7305
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7290
Beta-lactamase P00811 AMPC_ECOLI Escherichia coli 3 0.7274
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7266
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7262
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7233
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7232
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7222
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7218
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7214
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7212
Ethylene receptor 1 P49333 ETR1_ARATH Arabidopsis thaliana 3 0.7200
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7197
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7195
Acyl-CoA:acyl-CoA alkyltransferase Q8PDX2 OLEA_XANCP Xanthomonas campestris pv. campestris 3 0.7190
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7171
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 3 0.7168
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7164
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7143
YbaK/aminoacyl-tRNA synthetase-associated domain-containing protein Q5SHN1 Q5SHN1_THET8 Thermus thermophilus 3 0.7142
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7142
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7101
Glycogen phosphorylase, liver form P06737 PYGL_HUMAN Homo sapiens 3 0.7100
Isoflavone-7-O-methyltransferase 8 O24529 7OMT8_MEDSA Medicago sativa 4 0.7095
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7094
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7091
6-phosphogluconate dehydrogenase, decarboxylating P96789 6PGD_LACLM Lactococcus lactis subsp. cremoris 3 0.7080
Capsid protein VP1 O56137 O56137_9VIRU Adeno-associated virus - 6 4 0.7064
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 4 0.7051
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7047
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 4 0.7036
Ribonuclease TTHA0252 Q5SLP1 RNSE_THET8 Thermus thermophilus 3 0.7028
Isoleucine--tRNA ligase P56690 SYI_THET8 Thermus thermophilus 3 0.7026
Beta-secretase 2 Q9Y5Z0 BACE2_HUMAN Homo sapiens 3 0.7026
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7022
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7019
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7013
Cyclic GMP-AMP synthase Q8C6L5 CGAS_MOUSE Mus musculus 4 0.7008
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 4 0.7005
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7003
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.7003
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7001

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